The proposed work is to be done in three areas: 1) The biosynthetic route to nicotine via dihydronicotinic acid will be investigated. The imidazolide of 1,4-dihydroniotinic acid will be studied in its reaction with delta1-pyrroline-1-oxide and efforts will be made to realize a synthesis of nicotine from these constituents. 2) The biosynthetic route to the indole alkaloids will be investigated. Efforts will be made to prepare the 2-vinylindole-dihydropyridine system thought to be the biological intermediate in indole alkaloid biosynthesis. If this intermediate can be prepared, its application in the in vitro preparation of indole alkaloids will be evaluated. 3) The oxidative photoaddition of p-benzoquinone to 1,4- dienes will be investigated. This photochemistry will be initiated with an argon ion laser. If bicyclic (4.2.1) peroxides can be formed by this approach, the method will be used in attempts to synthesize prostaglandins from polyunsaturated fatty acids.